Acetic Acid → 4-(Benzylamino)-1-methylcyclohexanol

HRID 509291Notes

Reaction equation

HRID 509291 reaction equation
[OH:1][C:2]1([CH3:9])[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl.CO>[CH2:10]([NH:17][CH:5]1[CH2:6][CH2:7][C:2]([CH3:9])([OH:1])[CH2:3][CH2:4]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 285394-Hydroxy-4-methylcyclohexanoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 674652054-(Benzylamino)-1-methylcyclohexanolYield 107.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

4-hydroxy-4-methylcyclohexanone (270 mg, 1.48 mmol) was dissolved in 1,2-dichloroethane (8.3 ml), followed by sequential addition of benzylamine (0.2 ml, 1.83 mmol), NaBH(OAc)3 (560 mg, 2.66 mmol), and acetic acid (0.1 ml, 1.66 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 72 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, and extracted with 5% MeOH/MC (50 ml×3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (10% MeOH/MC), to obtain 350 mg of yellow solid (96%).

Workup

  1. customThe resulting reaction liquid
  2. extractionextracted with 5% MeOH/MC (50 ml×3)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfollowed by filtration and concentration
  5. customthe residue thus obtained

Sources & evidence

ORD record
ord-a07764ba39b44831a5d247ea2f98d91b
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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